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Synthesis of 2′-Azido-2′,3′-didehydro-2′,3′-dideoxythymidine

✍ Scribed by Mikhailopulo, Igor A. ;Zaitseva, Galina V. ;Vaaks, Elena V. ;Balzarini, Jan ;De Clercq, Eric ;Rosemeyer, Helmut ;Seela, Frank

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 598 KB
Volume: 1993
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199319930185

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✦ Synopsis

Abstract

Compound 15 – the 2′‐azido analog of the anti‐HIV compound 2′,3′‐didehydro‐2′,3′‐dideoxythymidine – was synthesized. Treatment of 5′‐O‐trityl‐β‐D‐ribofuranosylthymine (1) with DAST or MSTF gave the 2,2′‐anhydro derivative 2. The latter and its 3′‐O‐benzoate 3 were used for the synthesis of the 2′‐azido‐2′‐deoxy derivatives 4 and 5. Two routes to the synthesis of 15 from 5 were investigated. (i) Treatment of 5 with DAST gave a mixture of the 5′‐O‐trityl derivatives 12 and 13 as well as 1‐(2‐azido‐2,3‐dideoxy‐3‐fluoro‐β‐D‐xylofuranosyl)thymine (16) along with 2,3′‐anhydro derivative 14 (2%). Detritylation of the mixture yielded 15 (39%) and 16 (12%). (ii) Mesylation of 5 gave 17 which yielded 15 upon saponification and detritylation. Compound 15 showed moderate inhibitory activity against HIV‐1 and HIV‐2 in MT‐4 cells.

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